Cortona: worth it?

We can't tell what you'd be giving up to see Cortona instead. But I wanted particularly to see Fra Angelico's "Annunciation". The museum did not disappoint, although it's a small place. There were lots of good things to see in the museum. The town had some of the charm of San Gimigiano, but is perhaps only 30% as big, and did not seem heavily touristed. It was, as usual in hilltowns, tricky to find a legal parking place. I certainly endorse a visit. It can't be listed as a must-see hilltown, but I'm glad we went.

We combined this car-day-outing from Sinalunga with a prepaid appointment for formal lunch and tour of the Aviognesi Winery, which was one of the highlights of our visit. We also spent a few hours at Castiglione del Lago, which was especially nice on a sweltering day (i.e. it's on a lake, and even has a beach, which we skipped.) I later read that there's good food in C.D.L., but we couldn't eat another thing.

I think you owe it to yourself to visit at least ONE must-see hilltown, even if it is crowded. A middle-choice (I mean, less famous than Siena, but still very attractive, and not quite as jammed) is Orvieto. I would not go to Siena and San Gimigniano on the same day.

Good points Tim. We'll be coming from a week in Montepulciano where we'll be doing day trips in Val d'Orcia and up towards Volterra and Chianti, so we'll be seeing plenty of hill towns. The only thing we're potentially giving up is another day in Umbria and sights down there.

I'm not a wine nut, but an unusual thing about Aviognesi is that they own vineyards in more than one province. You can stand in two of them at once, straddling the formal and important (I mean, in wine appelation) regulatory line. I'm sure it serves their marketing to emphasize their presence in Tuscany. Anyway, a lot of our driving that day was in Umbria.

We stayed in Cortona for three nights and had a view of the valley from our hotel and day tripped from there and walked the town in the evenings and really enjoyed it,kind of laid back.Good restaurants in the town center.
Mike

Our American host in Montalcino made a little itinerary for us and recommended we spend our time elsewhere, such as the Sant' Animo Abbey and Rocca d' Orcia. We made a driving loop stopping at will for photos and discovering quaint villages away from the tourists. He said really the biggest deal that Cortona has going for it is the fact that "Under the Tuscan Sun" was filmed there. We've not regretted our choice.